AU2004261591A1 - Imidazo-pyrimidines and triazolo-pyrimidines: benzodiazepine receptor ligands - Google Patents

Info

Publication number

AU2004261591A1

AU2004261591A1 AU2004261591A AU2004261591A AU2004261591A1 AU 2004261591 A1 AU2004261591 A1 AU 2004261591A1 AU 2004261591 A AU2004261591 A AU 2004261591A AU 2004261591 A AU2004261591 A AU 2004261591A AU 2004261591 A1 AU2004261591 A1 AU 2004261591A1

Authority

AU

Australia

Prior art keywords

imidazol

triazolo

ylmethyl

propyl

pyrimidine

Prior art date

2003-07-25

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Abandoned

Links

• Espacenet
• Global Dossier
• Discuss

• 239000003446 ligand Substances 0.000 title description 15
• 150000005237 imidazopyrimidines Chemical class 0.000 title description 8
• 102000004300 GABA-A Receptors Human genes 0.000 title description 4
• 108090000839 GABA-A Receptors Proteins 0.000 title description 4
• 150000001875 compounds Chemical class 0.000 claims description 333
• 102000027484 GABAA receptors Human genes 0.000 claims description 124
• 108091008681 GABAA receptors Proteins 0.000 claims description 124
• 239000000203 mixture Substances 0.000 claims description 95
• -1 nitro, cyano, amino Chemical group 0.000 claims description 94
• 125000000217 alkyl group Chemical group 0.000 claims description 81
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 67
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 63
• 229910052736 halogen Inorganic materials 0.000 claims description 63
• 125000001424 substituent group Chemical group 0.000 claims description 63
• 150000002367 halogens Chemical class 0.000 claims description 62
• 229910052739 hydrogen Inorganic materials 0.000 claims description 56
• 238000000034 method Methods 0.000 claims description 56
• 125000003545 alkoxy group Chemical group 0.000 claims description 55
• 239000001257 hydrogen Substances 0.000 claims description 55
• 150000003839 salts Chemical class 0.000 claims description 53
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 49
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 46
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 44
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 42
• 230000027455 binding Effects 0.000 claims description 42
• 230000000694 effects Effects 0.000 claims description 42
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 38
• 150000002431 hydrogen Chemical class 0.000 claims description 37
• 229910052757 nitrogen Inorganic materials 0.000 claims description 36
• 238000003556 assay Methods 0.000 claims description 35
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 35
• 125000001188 haloalkyl group Chemical group 0.000 claims description 34
• 102000005962 receptors Human genes 0.000 claims description 34
• 108020003175 receptors Proteins 0.000 claims description 34
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 31
• 239000000523 sample Substances 0.000 claims description 28
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 26
• 125000004076 pyridyl group Chemical group 0.000 claims description 25
• 238000012360 testing method Methods 0.000 claims description 25
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 21
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 21
• QLOWGDIISXJREF-UHFFFAOYSA-N [1,2,4]triazolo[1,5-c]pyrimidine Chemical compound C1=CN=CN2N=CN=C21 QLOWGDIISXJREF-UHFFFAOYSA-N 0.000 claims description 20
• XUFCBCHWTOAVAA-UHFFFAOYSA-N [1,2,4]triazolo[4,3-c]pyrimidine Chemical compound C1=CN=CN2C=NN=C21 XUFCBCHWTOAVAA-UHFFFAOYSA-N 0.000 claims description 20
• 208000019901 Anxiety disease Diseases 0.000 claims description 19
• 229910052799 carbon Inorganic materials 0.000 claims description 19
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 19
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 19
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
• 125000005518 carboxamido group Chemical group 0.000 claims description 17
• 239000008194 pharmaceutical composition Substances 0.000 claims description 17
• 208000019116 sleep disease Diseases 0.000 claims description 17
• 230000036506 anxiety Effects 0.000 claims description 15
• 239000003814 drug Substances 0.000 claims description 15
• 125000001153 fluoro group Chemical group F* 0.000 claims description 15
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
• 239000003795 chemical substances by application Substances 0.000 claims description 13
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 12
• 229910052760 oxygen Inorganic materials 0.000 claims description 12
• 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 11
• 150000005215 alkyl ethers Chemical class 0.000 claims description 11
• 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims description 11
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 10
• 208000024827 Alzheimer disease Diseases 0.000 claims description 10
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
• 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims description 10
• 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 9
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 9
• 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 9
• 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims description 9
• 208000020685 sleep-wake disease Diseases 0.000 claims description 8
• FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 claims description 7
• 208000000044 Amnesia Diseases 0.000 claims description 7
• 230000007831 electrophysiology Effects 0.000 claims description 7
• 238000002001 electrophysiology Methods 0.000 claims description 7
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 7
• 230000006403 short-term memory Effects 0.000 claims description 7
• 125000000335 thiazolyl group Chemical group 0.000 claims description 7
• 125000001544 thienyl group Chemical group 0.000 claims description 7
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
• 238000005406 washing Methods 0.000 claims description 7
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
• GFFVZNWKFXBANZ-UHFFFAOYSA-N triazolo[1,5-c]pyrimidine Chemical compound [C]1=NC=CC2=CN=NN12 GFFVZNWKFXBANZ-UHFFFAOYSA-N 0.000 claims description 6
• UYUZKXAGLYQINB-UHFFFAOYSA-N 2-[1-[(8-propyl-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl)methyl]imidazol-2-yl]pyridine-3-carbonitrile Chemical compound N1=CN2N=CN=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1C#N UYUZKXAGLYQINB-UHFFFAOYSA-N 0.000 claims description 5
• CIAROHKHYKMXOX-UHFFFAOYSA-N 7-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]-1-methyl-8-propylimidazo[1,5-c]pyrimidine Chemical compound N1=CN2C=NC(C)=C2C(CCC)=C1CN1C=CN=C1C1=CC=CC(F)=N1 CIAROHKHYKMXOX-UHFFFAOYSA-N 0.000 claims description 5
• AFVWKPXVQGAVPE-UHFFFAOYSA-N 7-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]-8-propylimidazo[1,2-c]pyrimidine Chemical compound N1=CN2C=CN=C2C(CCC)=C1CN1C=CN=C1C1=CC=CC(F)=N1 AFVWKPXVQGAVPE-UHFFFAOYSA-N 0.000 claims description 5
• 230000004075 alteration Effects 0.000 claims description 5
• 238000000376 autoradiography Methods 0.000 claims description 5
• 239000013068 control sample Substances 0.000 claims description 5
• 238000004519 manufacturing process Methods 0.000 claims description 5
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 5
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 5
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
• VNRCPYKSCJJOCU-UHFFFAOYSA-N 3-(difluoromethyl)-7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-8-propyl-[1,2,4]triazolo[4,3-c]pyrimidine Chemical compound N1=CN2C(C(F)F)=NN=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F VNRCPYKSCJJOCU-UHFFFAOYSA-N 0.000 claims description 4
• HRETYXMMIJBZRN-UHFFFAOYSA-N 6-[1-[(8-propyl-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl)methyl]imidazol-2-yl]pyridine-2-carbonitrile Chemical compound N1=CN2N=CN=C2C(CCC)=C1CN1C=CN=C1C1=CC=CC(C#N)=N1 HRETYXMMIJBZRN-UHFFFAOYSA-N 0.000 claims description 4
• IPXNSCRXLXHBIZ-UHFFFAOYSA-N 7-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]-5-methyl-8-propylimidazo[1,2-c]pyrimidine Chemical compound N1=C(C)N2C=CN=C2C(CCC)=C1CN1C=CN=C1C1=CC=CC(F)=N1 IPXNSCRXLXHBIZ-UHFFFAOYSA-N 0.000 claims description 4
• UWTLXBIEGTWTMZ-UHFFFAOYSA-N 7-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]-8-propylimidazo[1,2-c]pyrimidine-2-carbonitrile Chemical compound N1=CN2C=C(C#N)N=C2C(CCC)=C1CN1C=CN=C1C1=CC=CC(F)=N1 UWTLXBIEGTWTMZ-UHFFFAOYSA-N 0.000 claims description 4
• 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 4
• 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 4
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 4
• 230000003389 potentiating effect Effects 0.000 claims description 4
• ZFCHNZDUMIOWFV-UHFFFAOYSA-N pyrimidine-2-carboxylic acid Chemical compound OC(=O)C1=NC=CC=N1 ZFCHNZDUMIOWFV-UHFFFAOYSA-N 0.000 claims description 4
• 230000001225 therapeutic effect Effects 0.000 claims description 4
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 3
• XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 3
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 3
• 125000001624 naphthyl group Chemical group 0.000 claims description 3
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 3
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
• 239000006188 syrup Substances 0.000 claims description 3
• 235000020357 syrup Nutrition 0.000 claims description 3
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 2
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
• GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims description 2
• HMHIPFOQWVGGCP-UHFFFAOYSA-N 7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-8-propyl-[1,2,4]triazolo[4,3-c]pyrimidine Chemical compound N1=CN2C=NN=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F HMHIPFOQWVGGCP-UHFFFAOYSA-N 0.000 claims description 2
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 2
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 2
• 239000002775 capsule Substances 0.000 claims description 2
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
• 230000003834 intracellular effect Effects 0.000 claims description 2
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
• WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical class [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
• UOKMJNZCIDAVIK-UHFFFAOYSA-N C(CC)C=1N=C2N(C=NC=C2)N1 Chemical compound C(CC)C=1N=C2N(C=NC=C2)N1 UOKMJNZCIDAVIK-UHFFFAOYSA-N 0.000 claims 2
• OQPDWSOJKINQLM-UHFFFAOYSA-N [1,2,4]triazolo[1,5-c]pyrimidin-2-amine Chemical compound C1=CN=CN2N=C(N)N=C21 OQPDWSOJKINQLM-UHFFFAOYSA-N 0.000 claims 2
• 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims 1
• 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims 1
• IZSCGZKYJYEHCE-UHFFFAOYSA-N 2-(ethoxymethyl)-7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidine Chemical compound N1=CN2N=C(COCC)N=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F IZSCGZKYJYEHCE-UHFFFAOYSA-N 0.000 claims 1
• ZVJRJPHEWFGMAX-UHFFFAOYSA-N 2-[(methylideneamino)-[1-[(3-methyl-8-propyl-[1,2,4]triazolo[4,3-c]pyrimidin-7-yl)methyl]imidazol-2-yl]methylidene]pent-3-enenitrile Chemical compound N1=CN2C(C)=NN=C2C(CCC)=C1CN1C=CN=C1C(N=C)=C(C=CC)C#N ZVJRJPHEWFGMAX-UHFFFAOYSA-N 0.000 claims 1
• UUIOMTRXMKJVRQ-UHFFFAOYSA-N 2-[1-[(2-methyl-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl)methyl]imidazol-2-yl]-1,3-thiazole Chemical compound N1=CN2N=C(C)N=C2C(CCC)=C1CN1C=CN=C1C1=NC=CS1 UUIOMTRXMKJVRQ-UHFFFAOYSA-N 0.000 claims 1
• DXFPPOJKGNNLKF-UHFFFAOYSA-N 2-[1-[[8-(3-fluoropropyl)-[1,2,4]triazolo[4,3-c]pyrimidin-7-yl]methyl]imidazol-2-yl]pyridine-3-carbonitrile Chemical compound N1=CN2C=NN=C2C(CCCF)=C1CN1C=CN=C1C1=NC=CC=C1C#N DXFPPOJKGNNLKF-UHFFFAOYSA-N 0.000 claims 1
• SBAWYMUGSDAFIP-UHFFFAOYSA-N 2-ethyl-7-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]-5-methyl-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidine Chemical compound N1=C(C)N2N=C(CC)N=C2C(CCC)=C1CN1C=CN=C1C1=CC=CC(F)=N1 SBAWYMUGSDAFIP-UHFFFAOYSA-N 0.000 claims 1
• MAMNCFUENSXJOF-UHFFFAOYSA-N 2-methyl-8-propyl-7-[(2-pyridin-2-ylimidazol-1-yl)methyl]-[1,2,4]triazolo[1,5-c]pyrimidine Chemical compound N1=CN2N=C(C)N=C2C(CCC)=C1CN1C=CN=C1C1=CC=CC=N1 MAMNCFUENSXJOF-UHFFFAOYSA-N 0.000 claims 1
• CGUKQGIMXXFLSP-UHFFFAOYSA-N 3-ethyl-7-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]-5-methyl-8-propyl-[1,2,4]triazolo[4,3-c]pyrimidine Chemical compound N1=C(C)N2C(CC)=NN=C2C(CCC)=C1CN1C=CN=C1C1=CC=CC(F)=N1 CGUKQGIMXXFLSP-UHFFFAOYSA-N 0.000 claims 1
• UERUEYQWZYJQJC-UHFFFAOYSA-N 3-methyl-8-propyl-7-[(2-pyridin-2-ylimidazol-1-yl)methyl]-[1,2,4]triazolo[4,3-c]pyrimidine Chemical compound N1=CN2C(C)=NN=C2C(CCC)=C1CN1C=CN=C1C1=CC=CC=N1 UERUEYQWZYJQJC-UHFFFAOYSA-N 0.000 claims 1
• SEEDBSFYNSDULV-UHFFFAOYSA-N 6-[1-[[8-(3-fluoropropyl)-[1,2,4]triazolo[4,3-c]pyrimidin-7-yl]methyl]imidazol-2-yl]pyridine-2-carbonitrile Chemical compound N1=CN2C=NN=C2C(CCCF)=C1CN1C=CN=C1C1=CC=CC(C#N)=N1 SEEDBSFYNSDULV-UHFFFAOYSA-N 0.000 claims 1
• CBFPVQBDUIONAG-UHFFFAOYSA-N 7-[[2-(2,5-difluorophenyl)imidazol-1-yl]methyl]-8-ethyl-[1,2,4]triazolo[1,5-c]pyrimidine Chemical compound N1=CN2N=CN=C2C(CC)=C1CN1C=CN=C1C1=CC(F)=CC=C1F CBFPVQBDUIONAG-UHFFFAOYSA-N 0.000 claims 1
• LBBRUTMMONIDJW-UHFFFAOYSA-N 7-[[2-(2,5-difluorophenyl)imidazol-1-yl]methyl]-8-ethyl-[1,2,4]triazolo[4,3-c]pyrimidine Chemical compound N1=CN2C=NN=C2C(CC)=C1CN1C=CN=C1C1=CC(F)=CC=C1F LBBRUTMMONIDJW-UHFFFAOYSA-N 0.000 claims 1
• MKVAHRVYXFGFIW-UHFFFAOYSA-N 7-[[2-(2,6-difluorophenyl)imidazol-1-yl]methyl]-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidine Chemical compound N1=CN2N=CN=C2C(CCC)=C1CN1C=CN=C1C1=C(F)C=CC=C1F MKVAHRVYXFGFIW-UHFFFAOYSA-N 0.000 claims 1
• GFWPDWYNKPMUCK-UHFFFAOYSA-N 7-[[2-(2,6-difluorophenyl)imidazol-1-yl]methyl]-8-propylimidazo[1,2-c]pyrimidine Chemical compound N1=CN2C=CN=C2C(CCC)=C1CN1C=CN=C1C1=C(F)C=CC=C1F GFWPDWYNKPMUCK-UHFFFAOYSA-N 0.000 claims 1
• GZJOODXEUFJDCY-UHFFFAOYSA-N 7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-2-(methoxymethyl)-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidine Chemical compound N1=CN2N=C(COC)N=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F GZJOODXEUFJDCY-UHFFFAOYSA-N 0.000 claims 1
• QEWKYEIJIPNJHO-UHFFFAOYSA-N 7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-2-methyl-8-(3-phenylmethoxypropyl)-[1,2,4]triazolo[1,5-c]pyrimidine Chemical compound C1=CN=C(C=2C(=CC=CN=2)F)N1CC=1N=CN2N=C(C)N=C2C=1CCCOCC1=CC=CC=C1 QEWKYEIJIPNJHO-UHFFFAOYSA-N 0.000 claims 1
• SPIKZNVEROZJMT-UHFFFAOYSA-N 7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-3-methoxy-5-methyl-8-propyl-[1,2,4]triazolo[4,3-c]pyrimidine Chemical compound N1=C(C)N2C(OC)=NN=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F SPIKZNVEROZJMT-UHFFFAOYSA-N 0.000 claims 1
• DNRXICIPOQCKBX-UHFFFAOYSA-N 7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-3-methyl-8-propyl-[1,2,4]triazolo[4,3-c]pyrimidine Chemical compound N1=CN2C(C)=NN=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F DNRXICIPOQCKBX-UHFFFAOYSA-N 0.000 claims 1
• DCRXEJZBQJKWSR-UHFFFAOYSA-N 7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-8-(methoxymethyl)-3-methyl-[1,2,4]triazolo[4,3-c]pyrimidine Chemical compound N1=CN2C(C)=NN=C2C(COC)=C1CN1C=CN=C1C1=NC=CC=C1F DCRXEJZBQJKWSR-UHFFFAOYSA-N 0.000 claims 1
• ZTBYDJXUPTZYBF-UHFFFAOYSA-N 7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-8-propyl-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-c]pyrimidine Chemical compound N1=CN2N=C(C(F)(F)F)N=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F ZTBYDJXUPTZYBF-UHFFFAOYSA-N 0.000 claims 1
• YVNMREPZHJKGGJ-UHFFFAOYSA-N 7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-8-propyl-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-c]pyrimidine Chemical compound N1=CN2C(C(F)(F)F)=NN=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F YVNMREPZHJKGGJ-UHFFFAOYSA-N 0.000 claims 1
• DUCQNVVDVIJXFQ-UHFFFAOYSA-N 7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidine Chemical compound N1=CN2N=CN=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F DUCQNVVDVIJXFQ-UHFFFAOYSA-N 0.000 claims 1
• JUXFIJBURSYEMS-UHFFFAOYSA-N 7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidine-2-carbonitrile Chemical compound N1=CN2N=C(C#N)N=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F JUXFIJBURSYEMS-UHFFFAOYSA-N 0.000 claims 1
• MSAMDYNIRBHZAJ-UHFFFAOYSA-N 7-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-8-propyl-[1,2,4]triazolo[4,3-c]pyrimidine-3-carbonitrile Chemical compound N1=CN2C(C#N)=NN=C2C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F MSAMDYNIRBHZAJ-UHFFFAOYSA-N 0.000 claims 1
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